The Legend of Sleepy Hollow in Pop Culture and Beyond


Monday, 11/28/2016 5:40pm

In 1820, Washington Irving made Sleepy Hollow an international pop culture sensation with the publication of The Legend of Sleepy Hollow—and it’s been firmly lodged in the public’s imagination ever since. Hundreds of interpretations of the tale for the big and small screen, stage adaptations, songs—and, yes, even opera—have helped to make the town one of America’s most famous small villages. Here are just a few ways the classic story has been retold since its publication.

One of the first full-length feature film adaptations of Irving’s tale starred Will Rogers. The 1922 silent movie The Headless Horseman was filmed on location for authenticity, but stretched the narrative by adding a subplot about Ichabod Crane nearly getting tarred and feathered by an angry mob.

In 1949 Disney told Irving’s story in The Adventures of Ichabod and Mr. Toad. Narrated by Bing Crosby, the cartoon gives Ichabod a rather happy ending—it’s discovered that he’s living in a far-off country, married to a rich widow, with children who look like him—but has still managed to terrify and delight children ever since its debut.

Fast forward to 1999, and the tale took on a new dimension when the famed horror and fantasy director Tim Burton presented a live-action version starring Johnny Depp. Sleepy Hollow took some liberties with the story—including changing Ichabod Crane’s profession from teacher to police constable, making Lady Van Tassel a witch, and turning Ichabod into a hero who breaks the Headless Horseman’s curse—but kept the creepy tone of the story and wound up winning an Academy Award for production design.

More recently, The Legend of Sleepy Hollow has made a splash on the small screen with Fox’s Sleepy Hollow. The series reimagines Ichabod Crane as Revolutionary War double-agent who wakes up 250 years later to find that the Headless Horseman is on the loose in present-day Sleepy Hollow.

Irving’s famous legend has also made its way onto the stage in several productions, including a run on Broadway with a 1948 musical, and several composers have tried their hand at turning the story into an opera. The Monotones also felt the lyrical nature of the story—they released a DooWop song called “The Legend of Sleepy Hollow.”

The impact of the town and Irving’s story are so widespread that they’ve even made their way out of fiction and song and into “real” life. Visit Falls Church, Virginia, and you’ll find Sleepy Hollow Road, Crane Drive, Ichabod Place, Horseman Lane, Sleepy Hollow Park, and Sleepy Hollow Bath & Racquet Club. In Pearland, Texas, you can drive down Washington Irving Drive, Sleepy Hollow Drive, Crane Drive, Tarrytown Lane, and Brom Bones Boulevard. And in Illinois and California you’ll find towns named, you guessed it, Sleepy Hollow.

Find out more about Washington Irving—visit his home at Sunnyside in Tarrytown and discover how he lived.

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